Upside.com Wooing Businesses With Elaborate Gifts

I have used Upside.com for business trips in the past with mixed results. I was shocked and amazed at what they sent me to remind me of why I should book business travel with them. Can you believe what Upside sent me?

Past Experience with Upside

Upside is an OTA (Online Travel Agency) started by a former Priceline founder Jay Walker that targets business travelers. By pairing consolidator airline tickets and hotel agreements, the company allows travelers flexibility when plans change but they don’t make the bookings entirely transparent. Consolidator fares cause problems for frequent flyers who rely on earning elite-qualifying dollars as the amount paid does not carry over into EQD, MQD, or PQD (whichever your particular airline calls them).

The prices are typically in line with what is found at other OTAs. Since Upside uses consolidator fares with opaque costs, they pay less for the airfare (which is why you don’t get PQDs) and mark it up to retail rates. They also use their commission from hotel bookings to incentivize travelers for their business. Sometimes this is a pair of Bose headphones, an Amazon Echo or gift cards. If tickets you buy for business preclude you from earning benefits, or you prefer these items instead of miles (which have become harder and harder to use) then perhaps this works for you. It didn’t align with my own preferences.

During a United status challenge I booked a three-day trip for about $1200 through Upside.com. Comparing it to other OTAs, my flights ran about $600 and my hotel stay was about the same – it is a very expensive market. As Upside.com was competitive and I was incentivized, why would I book elsewhere?

I chatted with Upside customer service prior to booking to ensure the ticket would earn normally. The agent was not aware of the limitations of the ticket and told me they would credit properly. When the PQDs didn’t post, I reached out to them again, they discovered the error and to make it right, they credited the entire trip. I want to be clear on this, I protested several times – the credit of a $1200 trip in its entirety was far too generous for the simple mistake made. I should also note that this was for my day job not connected with blogging, there is no way they could have known that I was a travel blogger.

Survey

Once the calendar turned to 2018, the company sent out a survey and the response (purportedly) went straight back to the executive team. The survey asked several poignant questions, among them how many business trips I booked for myself last year (more than 21 was the category I selected) and how many for others (same answer). They then asked if I intended to book more or less than the year before with Upside.com. I indicated that I would book less (than my one trip) in the coming year. Then they asked why with an essay response form. I indicated that without earning hotel or flight status qualifiers I just couldn’t see this replacing my current modus operandi ignoring the ethical complexity of booking business trips that personally enrich me.

I want to be clear that their solution to the original problem was more than sufficient to make the situation right. In fact, it was too generous. If I didn’t earn credit for a single flight and stay, no big deal. When they ask about moving forward, receiving the associated credit to my hotel and flight is too big of an issue for me, it is a deal breaker. You can toss headphones at me, Amazon gift cards, whatever you want – it’s just not going to work for me personally. Until status earning on their platform changes, I will continue to book elsewhere. I’m not mad about it, they shouldn’t be either – their model just won’t work for me but maybe it will for others in my business who travel infrequently.

Can You Confirm Your Address

Following my survey response I received an email from someone at Upside corporate asking to confirm my business mailing address. I supplied it and thought nothing more of it. Perhaps a thank you letter for last year’s business or a promotional packet discussing the benefits of using Upside. I expected I would receive something along those lines. Instead I found this waiting for me when I returned to my desk from a trip.

Awfully large care packageHand-written noteFor the officeK-cups, not my flavor, but someone in the office will drink it I am sure.Amazon Echo, very generous.Umbrellas for our teamI love notebooks, this was the hardest to give to other staff members.All purple everythingA few handy chargers, also in purplePhone attachments, I don’t use them but a couple of other staff members gobbled this up.A full-sized Keurig 2.0 – also in purple.

If I had to guess, and of course I do, I would say that the value of this box with shipping was in the range of $400. That’s pretty generous and reminds travel bookers like our admin team that we should be getting something back for our travel spend. It was unexpected and really impressive, but will it lead to different results for Upside?

Will It Change Our Booking Pattern?

For my travel, it still won’t change booking style. When Pointshound and Rocketmiles both came out a few years ago, Pointshound paid out smaller mileage bonuses for hotel bookings, but they still counted towards elite status. I gave Pointshound 100% of my hotel bookings because I have to book somewhere, why not book with Pointshound?

Pointshound lost the ability to avoid elite third-party booking exemptions and sadly, they lost my business too. I occasionally continue to utilize Rocketmiles and Pointshound when I have already re-qualified for a program and the price is the same, or a preferred chain is unavailable for a given date and market.

However…

My business has evolved and my group routinely books hotels for staff members who rarely travel for work and do not generally care about miles and points. Our company gets nothing for these bookings now, though we’ve tried a number of different methods to recoup benefits for their spend. Our hotel spend varies between $20,000 and $100,000/month for our small team – it’s a lot of time on the road. For our admin who carries out the bookings, however, it makes a lot of sense to start booking through Upside as opposed to shopping elsewhere. The flexibility Upside offers is great and we receive no incentive for our business hotel spend without them. Now, the company can earn gift cards used to incentivize staff who spend a lot of time away from home. For those bookings, I expect we will start to use Upside to secure hotels now that we can do so without an accompanying flight.

While I would say that bribery doesn’t work, generosity seems to. It’s a reminder too that we are leaving money on the table as a company and that’s just bad business. I would, however, like to clarify that there is a thin line between bribery and generosity. Upside may be teetering on the line with this elaborate care package.

What do you think? Is Upside.com’s generosity fair, over-the-top or normal?

About Author

Kyle Stewart

Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, Travel Codex and many other media outlets. He is also cofounder of PenAndPassport.com. He focuses on using miles and points to provide a premium experience for his wife and daughter.

Creative screen name. I doubt that they targeted me outside of ticket/hotel spend and I definitely voiced my frustration when I had been given incorrect information but from my work phone, work email. It would be difficult to connect the dots. You are entitled to your opinion, all of them.

Hi, Kyle. By way of introduction, my name is Genevieve, and I’m on the growth team at Upside. We saw your blog post and wanted to reach out with a little context about what we’re up to and what’s new from Upside.

First of all, thank you for the feedback. We know airline miles and hotel points are a big deal to a lot of business travelers, and we’ve been making good progress in that area. We’re excited to let you know that we offer PQDs, PQMs and points on all United Airlines flights and qualifying miles on all flights on Upside. We still have work to do on hotel points, but we’re optimistic. As you know, it’s rare that online travel sellers can provide hotel points. What makes us different – and hopeful – is we serve only high yield business travelers, which are much more attractive to hotels than leisure bargain hunters that make up so much of OTA sales.

Our focus on business travelers is one of our key differentiators along with our commitment to providing world-class service at no extra cost. We’re glad you had such a good experience with our team of “Navigators,” who clearly went above and beyond refunding your trip. (Quite generous!) I can’t say we do that often, but it’s indicative of building a high service culture that will set the stage for our growth.

So far, so good. Our NPS is 73, which puts us in the world class category, and we recently won a Feefo Gold Service award, an independent seal of excellence that recognises businesses for delivering exceptional experiences, as rated by real customers. We are also very proud to have been named one of the Top 50 Companies to Work for in 2018 from Glassdoor.

It was fun for us to see you write about the big box of purple “stuff” you got from us. You were part of a very small test we ran to see if we could turn an individual traveler at a company into a whole lot of travelers from your company. After all, it’s natural for colleagues to ask, “Who is Upside?” and “Why did they send you all these things?” when a box like that arrives.

We continue to experiment with different ways to attract the attention of first-time customers. That’s why you’ve seen headphones and gift cards. We realize that it takes a lot to get noticed and stimulate a trial purchase. And, we also know the lifetime loyalty of a single business traveler is worth a lot of money.

We’re happy to talk on the phone anytime about our plans and, of course, how we can do a better job for you. Many new things will be coming soon. Please reach out to me anytime: g@upside.com.

Thanks for reaching out Genevieve, I think it’s a really smart plan, and will probably work great for getting the message out to the rest of my company where I wouldn’t have necessarily evangelized before.

Believe what you want, but all of my transactions and communications were from work email addresses and phone numbers – if they did, they would have had to search following a communication with their customer support team. It’s possible that someone in customer support googled my name and found the blog then sent it up the chain of command to send me a gift, but respectfully, I think that’s a stretch. It makes more sense that they had one customer who spent $1200 on their first visit, was disappointed to the point of full refund, and they realized I hadn’t been back. But as always, you’re entitled to your opinion.